Divot

Derek Andersen
  • 4.9 (19)
  • BUSINESS
  • UPDATED WEEKLY

Divot brings you weekly conversations with the people building the future—founders, creators, athletes, and visionaries pushing the limits of business, technology, sports, and entertainment. We go beyond success stories to explore the real moments that define a journey—the risks, the failures, the breakthroughs, and the lessons that can help you on your path. Stories of people making their mark, and how you can too. New episodes every Wednesday. #DivotPodcast #Business #Tech #Sports #Entertainment #Innovation

  1. #40: How Filevine Founder Ryan Anderson Built a $3B Legal AI Platform

    3D AGO

    #40: How Filevine Founder Ryan Anderson Built a $3B Legal AI Platform

    Before building one of the fastest-growing legal technology companies in the United States, Ryan Anderson was a practicing lawyer frustrated by deadlines, paperwork, and systems that made it easy to miss critical details. Instead of accepting the chaos of legal operations, he decided to build a better system. In this conversation with Derek Andersen, Ryan shares how that decision became Filevine, a legal tech platform now serving nearly 6,000 customers, employing more than 700 people, and generating more than $200 million in annual revenue. He explains how AI is transforming legal work and why technology can dramatically improve outcomes for lawyers and their clients. Ryan also opens up about rebuilding Filevine to become an AI-native company. From rewriting years of engineering work to navigating one of the fastest-moving industries in the world, he reflects on leadership, conviction, and what it takes to adapt when technology changes everything. The episode goes deeper into entrepreneurship, justice, and purpose, exploring why access to legal systems is expanding and why great lawyers will become even more powerful with AI. Follow Ryan - X (Twitter): https://x.com/ryanm_andersonFollow Derek - X (Twitter): https://twitter.com/derekjandersen Episode Partners:DelveDelve uses AI agents to handle SOC 2, ISO 27001, GDPR, and more - Divot listeners get $1,500 credits to get started: https://delve.co/deals/divot PulleyManage your cap table with intuitive tools built to help founders make informed decisions without breaking stride. https://tinyurl.com/PulleyPartner Timestamps:02:42 — What Filevine Actually Does (Legal AI Explained)04:08 — The Problem That Inspired Filevine05:03 — The Risk Conversation With His Wife09:03 — Meeting the Engineer Who Built the Vision11:56 — The Founder Mindset: “I’ll Figure It Out”18:20 — The Day Ryan Quit His Job22:14 — Rewriting Filevine for the AI Era25:41 — How AI Is Changing Software Teams31:28 — Why the Legal Industry Could Grow 100x44:55 — The Future of Law: AI Running Legal Work55:20 — The Mindset to Build a Billion-Dollar Company01:06:10 — Ryan’s Real Definition of Success Follow Divot:YouTube: https://www.youtube.com/@DivotpodX (Twitter): https://twitter.com/divotdotorgInstagram: https://www.instagram.com/divotpodTikTok: https://www.tiktok.com/@divotpodLinkedIn: https://www.linkedin.com/company/divotdotorg Hashtags:#RyanAnderson #LegalAI #LegalTech #Entrepreneurship #SaaS #ArtificialIntelligence #Leadership #Justice #Innovation #DivotPodcast

    1h 8m
  2. #39: How Master Mechanic Dave Bell Built an 8M-Follower YouTube Empire

    MAR 4

    #39: How Master Mechanic Dave Bell Built an 8M-Follower YouTube Empire

    Before becoming one of the most respected independent mechanics in the United States, Dave Bell was a young man battling addiction, jail time, and the fear of losing everything. Over the past 36 years, he rebuilt his life the same way he rebuilds engines, with discipline, precision, and relentless ownership. In this conversation, Dave shares how he grew from a one-bay storage unit during the 1990 recession into a 33,000-square-foot auto center with 35 employees, and how an unexpected leap into social media led to more than 8 million followers across YouTube, TikTok, and Instagram. He explains why opposition is an opportunity, how elite mechanics think, and why authenticity online outperforms any marketing budget. Dave also opens up about addiction, faith, jail, and the turning points that changed his trajectory. From reading Atlas Shrugged behind bars to building one of the largest independent automotive brands in the world, he reflects on agency, momentum, and the power of choosing who you become. The episode goes deeper into leadership, fatherhood, and legacy, exploring what it means to master yourself, redefine a misunderstood industry, and live by a simple philosophy: never let anyone else define who you are. Follow Dave - Instagram: https://www.instagram.com/davesautocenterFollow Derek - X (Twitter): https://twitter.com/derekjandersen Episode Partners:DelveDelve uses AI agents to handle SOC 2, ISO 27001, GDPR, and more - Divot listeners get $1,500 credits to get started: https://delve.co/deals/divotPulleyManage your cap table with intuitive tools built to help founders make informed decisions without breaking stride. https://tinyurl.com/PulleyPartner Timestamps:02:42 — From 300 Followers to 8 Million: The Unexpected Breakthrough09:07 — “Who Are You?” The Identity Wake-Up Call13:19 — A Mission Bigger Than Cars: Changing an Entire Industry16:55 — Fearless: What Separates Elite Mechanics from Everyone Else26:42 — “Don’t Ever Let Anyone Define You” (A Father’s Turning Point)33:14 — The 4 O’s: Turning Opposition Into Opportunity45:17 — Drugs, Fast Money & Walking Away Before It Was Too Late50:48 — Rock Bottom at 35: Addiction, Faith & Choosing a Different Path57:35 — Six Months in Jail & The Book That Rewired His Mind01:01:50 — The Hard Truth: The Moment You Blame, You Lose01:09:40 — Momentum, Waves & The “Perfect Soup” Theory of Life01:10:11 — In the End, Only One Thing Matters Follow Divot:YouTube: https://www.youtube.com/@DivotpodX (Twitter): https://twitter.com/divotdotorgInstagram: https://www.instagram.com/divotpodTikTok: https://www.tiktok.com/@divotpodLinkedIn: https://www.linkedin.com/company/divotdotorg Hashtags:#DaveBell #Entrepreneurship #AddictionRecovery #MechanicLife #Leadership #BusinessGrowth #SocialMediaSuccess #AtlasShrugged #PersonalDevelopment #Agency #Momentum #AutoIndustry #DivotPodcast

    1h 16m
  3. #38: Building Great Products, Product Leadership & the Future of Work with Tomer Cohen (LinkedIn)

    FEB 25

    #38: Building Great Products, Product Leadership & the Future of Work with Tomer Cohen (LinkedIn)

    Recorded at LinkedIn headquarters in Mountain View, this episode features Tomer Cohen, former Chief Product Officer of LinkedIn and one of the product leaders behind how over one billion professionals connect, work, and create economic opportunity at global scale. In conversation with Derek Andersen, Tomer breaks down what it takes to build great products inside large organizations, how LinkedIn evolved into a mobile-first platform, and what product leadership really means when operating at massive scale. The discussion expands into AI and the future of work, where Tomer explains the rise of the full-stack product builder, how AI is collapsing traditional roles across product, design, and engineering, and why builders who combine vision, empathy, and execution will define the next generation of companies. The episode closes with deeply personal reflections on growth mindset, restraint, resilience, faith, and the idea that true freedom lives in the space between stimulus and response. Follow Tomer - LinkedIn: https://www.linkedin.com/in/tomercohenFollow Derek - X (Twitter): https://twitter.com/derekjandersen Episode Partners:DelveDelve uses AI agents to handle SOC 2, ISO 27001, GDPR, and more - Divot listeners get $1,500 credits to get started: https://delve.co/deals/divot PulleyManage your cap table with intuitive tools built to help founders make informed decisions without breaking stride. https://tinyurl.com/PulleyPartner Timestamps:00:00 — Between Stimulus and Response: Where Freedom Truly Lives08:55 — Rebuilding LinkedIn for Mobile Before It Was Obvious11:02 — Turning LinkedIn Into a Daily Habit, Not a Transaction13:34 — Why Authentic Voices Beat Corporate Talk Every Time18:24 — Conviction Over Titles: Choosing Where to Make Impact20:28 — The Rider and the Elephant: How Organizations Really Move24:42 — What Separates a Good Product from a Truly Great One31:34 — Restraint: The Hidden Skill Behind Billion-Dollar Products35:09 — Slowing Down to Fix the Core Before Scaling39:12 — The Rise of the Full-Stack Product Builder42:02 — How AI Is Collapsing Roles and Restoring Meritocracy53:25 — The Truth About Success: There Are No Shortcuts59:55 — The Final Lesson: Choosing How You Respond Follow Divot:YouTube: https://www.youtube.com/@DivotpodX (Twitter): https://twitter.com/divotdotorgInstagram: https://www.instagram.com/divotpodTikTok: https://www.tiktok.com/@divotpodLinkedIn: https://www.linkedin.com/company/divotdotorg Hashtags:#TomerCohen #LinkedIn #ProductLeadership #BuildingGreatProducts #AI #FutureOfWork #ProductManagement #StartupLeadership #GrowthMindset #DivotPodcast

    1h 7m
  4. #37: AI, Venture Capital, Faith & The Future of Work with Mamoon Hamid (Kleiner Perkins)

    FEB 18

    #37: AI, Venture Capital, Faith & The Future of Work with Mamoon Hamid (Kleiner Perkins)

    Recorded on Sand Hill Road at the iconic offices of Kleiner Perkins, this episode features Mamoon Hamid, one of the most influential investors of this generation. Mamoon has backed category-defining companies, including Slack, Figma, Box, Yammer, Glean, Intercom, and more, and now serves as a partner stewarding one of Silicon Valley’s most historic venture firms. In conversation with Derek Andersen, Mamoon breaks down how great investors evaluate founders, why conviction starts with why, and what separates category creators from incremental startups. The discussion expands into AI, where Mamoon shares why this cycle is fundamentally different from every prior technology wave. He explains why AI is not just software but labor, how it’s reshaping productivity across professions, and why adoption and monetization are happening faster than ever, from copilots to autonomous agents transforming how work gets done. The episode closes with deeply personal reflections on resilience, immigration, parenting, faith, and purpose. Follow Mamoon - X (Twitter): https://x.com/mamoonha Follow Derek - X (Twitter): https://twitter.com/derekjandersen Episode Partners: Delve Delve uses AI agents to handle SOC 2, ISO 27001, GDPR, and more - Divot listeners get $1,500 credits to get started: https://delve.co/deals/divot Pulley Manage your cap table with intuitive tools built to help founders make informed decisions without breaking stride. https://tinyurl.com/PulleyPartner Timestamps: 00:00 — “God Is the Best of Planners” — Faith, Loss & Letting Go of Control 01:40 — Inside the Most Powerful Room in Silicon Valley (Why It’s Rarely Used) 05:05 — What Elite Investors Actually Listen For in Founder Pitches 06:55 — Why Metrics Don’t Matter If You Can’t Explain Your “Why” 10:30 — How Slack & Box Were Backed When the Market Didn’t Exist 14:25 — Why AI Is the Biggest Technology Shift in 30 Years 18:50 — AI Isn’t Software — It’s Labor (And That Changes Everything) 23:30 — The Future of Work: What Humans Will Do Better Than AI 27:10 — Leaving Your Own Firm to Rebuild a Legendary One 31:05 — The Apprenticeship Model That Built Venture Capital Giants 35:45 — Growing Up Between Germany & Pakistan — Lessons in Resilience 39:30 — How Do You Raise Resilient Kids in an Easy World? 42:55 — Why Sports Might Be the Best Teacher of Grit 49:55 — The Hajj: Witnessing the Best of Humanity Under Extreme Conditions 56:20 — Inshallah — Ambition, Failure & Accepting God’s Will 59:35 — How Mamoon Hamid Measures a Life Well Lived Follow Divot: YouTube: https://www.youtube.com/@Divotpod X (Twitter): https://twitter.com/divotdotorg Instagram: https://www.instagram.com/divotpod TikTok: https://www.tiktok.com/@divotpod LinkedIn: https://www.linkedin.com/company/divotdotorg Hashtags: #MamoonHamid #KleinerPerkins #VentureCapital #AI #FutureOfWork #Startups #Founders #FaithAndWork #Leadership #DivotPodcast

    1h 2m
  5. #36: AI Shopping, The Future of Commerce & Why Trust Matters More Than Tech

    FEB 11

    #36: AI Shopping, The Future of Commerce & Why Trust Matters More Than Tech

    Before becoming a leader at the intersection of fashion, retail, and technology, Julie Bornstein built her career through persistence, curiosity, and conviction. Early on, she broke into the industry by reaching out directly to designers she admired, setting the foundation for a career that would later span Nordstrom, Sephora, Stitch Fix, and multiple consumer technology companies shaping how people discover what they wear. In this conversation, Julie shares what she learned building and scaling consumer products and why fashion is one of the most complex categories for technology to understand. Julie also reflects on the rapid shift now underway in commerce, as AI begins to reshape how people search, discover, and decide. She discusses why traditional e-commerce search fails in taste-based categories, how large language models unlock new possibilities for personalization, and what this moment has in common with earlier platform shifts like social and mobile. The episode goes deeper into purpose and long-term thinking, exploring trust, incentive alignment, and how technology should serve people rather than manipulate them. Follow Julie - X (Twitter): https://x.com/juliebornsteinFollow Derek - X (Twitter): https://twitter.com/derekjandersen Episode Partners:DelveDelve uses AI agents to handle SOC 2, ISO 27001, GDPR, and more - Divot listeners get $1,500 credits to get started: https://delve.co/deals/divot PulleyManage your cap table with intuitive tools built to help founders make informed decisions without breaking stride. https://tinyurl.com/PulleyPartner Timestamps:02:18 — She Broke Into Fashion by Writing Letters (No Network, No Shortcuts)05:01 — The Business of Fashion Explained Simply (How Brands Really Make Money)06:40 — Why Online Shopping Became Overwhelming (Too Much Choice Kills Confidence)07:28 — Why Most Fashion Brands Fail (No Point of View, Wrong Pricing)10:29 — Who Really Decides Fashion Trends? (Luxury, Runways & Fast Fashion)14:28 — The Nordstrom Leader Who Saw E-Commerce Before Anyone Else16:03 — Why Stitch Fix Didn’t Work for People With Real Taste18:29 — Selling a Startup: 40K Customers vs 400M Users at Pinterest23:52 — The 3 Reasons She Sold Her Company (Price, Market Crash, Team)26:33 — Why ChatGPT Made AI Shopping Finally Possible30:49 — Why Fashion Search Is Broken (Taste-Based, Not Keyword-Based)34:10 — The Rule Behind Daydream: If the Customer Wins, We Win44:30 — The Legacy She Wants to Leave (Making Shopping Smarter & Better) Follow Divot:YouTube: https://www.youtube.com/@DivotpodX (Twitter): https://twitter.com/divotdotorgInstagram: https://www.instagram.com/divotpodTikTok: https://www.tiktok.com/@divotpodLinkedIn: https://www.linkedin.com/company/divotdotorgHashtags:#JulieBornstein #AIShopping #FutureOfCommerce #ConsumerAI #FashionTech #RetailInnovation #Startups #Founders #Technology #DivotPodcast

    47 min
  6. #35: Investing Before Consensus, The AI Shift & What Makes Great Founders Win

    FEB 4

    #35: Investing Before Consensus, The AI Shift & What Makes Great Founders Win

    Before becoming one of the most respected early-stage investors in Silicon Valley, Niko Bonatsos was an immigrant from Greece navigating academia, visas, and uncertainty while searching for opportunity in the United States. Over the next 15 years, he became a Managing Director at General Catalyst, investing in iconic companies like Snap and Discord and backing technical founders long before their ideas became obvious to the world. In this conversation, Niko shares what he learned investing through multiple technology cycles and why most successful companies don’t start with the right idea. Niko also reflects on the resurgence of San Francisco as the center of the AI revolution, how ChatGPT reshaped the startup landscape almost overnight, and why this moment feels similar to the early days of social networking and mobile. From recognizing momentum before metrics to investing in overlooked builders, he offers a rare inside look at how early-stage conviction is actually formed. The episode goes deeper into purpose and legacy, exploring immigration, perseverance, parenting, and how Niko measures a life well lived. Rather than chasing status, money, or permanence, he explains why helping deeply obsessed builders bring their dreams to life and empowering others along the way is the mark that truly matters. Follow Niko - X (Twitter): https://x.com/bonatsosFollow Derek - X (Twitter): https://twitter.com/derekjandersen Episode Partners:DelveDelve uses AI agents to handle SOC 2, ISO 27001, GDPR, and more - Divot listeners get $1,500 credits to get started: https://delve.co/deals/divot PulleyManage your cap table with intuitive tools built to help founders make informed decisions without breaking stride. https://tinyurl.com/PulleyPartner Timestamps:02:42 — Stanford & Silicon Valley: One Intertwined Ecosystem06:18 — Why Founders Keep Chasing the Same Startup Ideas07:37 — Investing Before Consensus: The Real Seed Advantage08:22 — Why Most Successful Companies Don’t Start With the Right Idea09:49 — San Francisco Is Back: The AI Gravity Shift13:24 — Why Niko Invested Early in Snap15:44 — Discord: How a Failed Startup Became a Generational Company18:42 — Talent Is Universal, Opportunity Is Not21:17 — The Signals That Make an Investor Lean In26:49 — Can AI Replace Venture Capitalists?31:30 — The Rise of Tiny Teams and Explosive Growth34:01 — Why Non-AI Companies Are Fighting a Knife Fight38:13 — Leaving General Catalyst: A New Chapter42:18 — Alexander the Great & the Question of Legacy48:19 — “Just Get Started”: The One Idea He’d Give Everyone50:51 — How Niko Measures a Life Well Lived Follow Divot:YouTube: https://www.youtube.com/@DivotpodX (Twitter): https://twitter.com/divotdotorgInstagram: https://www.instagram.com/divotpodTikTok: https://www.tiktok.com/@divotpodLinkedIn: https://www.linkedin.com/company/divotdotorg Hashtags:#NikoBonatsos #VentureCapital #AI #Startups #SiliconValley #EarlyStageInvesting #Founders #Snap #Discord #GeneralCatalyst #Entrepreneurship #Innovation #DivotPodcast

    54 min
  7. #34: Creativity, Obsession & Building Products That Change the World

    JAN 28

    #34: Creativity, Obsession & Building Products That Change the World

    Before becoming one of the most influential evangelists in the history of technology, Guy Kawasaki was part of Apple’s original Macintosh team, working directly with Steve Jobs during the early days of personal computing. His career has been defined by independent thinking, deep curiosity, and a lifelong commitment to building and evangelizing products that truly matter. In this conversation, Guy reflects on working with Steve Jobs, the difference between mission-driven and ego-driven leadership, and why the best products are built by people solving problems for themselves. He shares hard-earned lessons from Silicon Valley on creativity, obsession, grit, and what it really takes to build things that last. Guy also discusses his role as Chief Evangelist of Canva, the global design platform democratizing creativity for millions worldwide, and how recognizing great products early shaped his journey. From writing 18 books to advising startups and founders, he explains why authenticity consistently outperforms imitation in entrepreneurship and product building. The episode goes deeper into purpose and legacy, exploring learning later in life, embracing setbacks, redefining success, and measuring impact not by status or money, but by one simple idea: empowering people. Follow Guy - Instagram: https://www.instagram.com/guykawasakiFollow Derek - X (Twitter): https://twitter.com/derekjandersen Episode Partners:DelveDelve uses AI agents to handle SOC 2, ISO 27001, GDPR, and more - Divot listeners get $1,500 credits to get started: https://delve.co/deals/divot PulleyManage your cap table with intuitive tools built to help founders make informed decisions without breaking stride. https://tinyurl.com/PulleyPartner Timestamps:1:09 — Starting Surfing at 60: Obsession Beats Talent3:49 — Growing Up in Hawaii: Identity, Culture & Perspective6:44 — Everybody Has Something to Hide: Privacy, Signal & Freedom12:44 — Writing 18 Books: Why Most People Shouldn’t Write One16:57 — Build for Yourself: The Origin of Great Products18:20 — Working With Steve Jobs: Mission Over Ego19:40 — Mission-Driven vs Ego-Driven Leadership22:35 — The Halo Effect: Why You Should Be Skeptical of Authority27:22 — Steve Jobs vs Elon Musk: Focus vs Scale30:51 — Don’t Be the Next Steve Jobs. Be the First You33:08 — Finding Your Calling: Loving the Entire “Sandwich”46:31 — Jane Goodall: Purpose Without Retirement52:19 — Guy’s Golden Touch: Finding Gold Early57:24 — Grit as the Real Advantage58:25 — Family, Legacy & Measuring a Life Follow Divot:YouTube: https://www.youtube.com/@DivotpodX (Twitter): https://twitter.com/divotdotorgInstagram: https://www.instagram.com/divotpodTikTok: https://www.tiktok.com/@divotpodLinkedIn: https://www.linkedin.com/company/divotdotorg Hashtags:#GuyKawasaki #SteveJobs #ElonMusk #Apple #Canva #Entrepreneurship #Startups #Creativity #ProductBuilding #Leadership #Innovation #SiliconValley #Grit #Purpose #DivotPodcast

    1h 1m
  8. #33: Mastery, Craft & Surfing Giants - Shaping Boards That Defined Big Wave Surfing

    JAN 21

    #33: Mastery, Craft & Surfing Giants - Shaping Boards That Defined Big Wave Surfing

    Before becoming one of the most respected surfboard shapers in the world, Bob Pearson built his craft through obsession, experimentation, and more than six decades of hands-on learning. Since shaping his first board in 1964, Bob has remained committed to one belief: mastery is never finished. Over his career, Bob has shaped more than 100,000 surfboards, becoming a defining force in modern surfboard design and big wave surfing. From his factory in Santa Cruz, California, he has worked closely with legendary surfers including Laird Hamilton, Jay Moriarty, Jamie Mitchell, and others who pushed the limits at waves like Mavericks, Jaws, Waimea, Sunset, and Nazaré. His boards were featured throughout the film Chasing Mavericks, shaping the equipment ridden in the movie. The episode also explores Bob’s friendship with Jay Moriarty, the mindset required for big wave surfing, and the deeper meaning of surfing beyond performance, connection, community, mental health, and joy. At 77 years old, Bob still works nearly every day, driven by curiosity, gratitude, and a lifelong passion for the ocean. Follow Bob - Instagram: https://www.instagram.com/pearsonarrow Follow Derek - X (Twitter): https://twitter.com/derekjandersen Episode Partners: Delve Delve uses AI agents to handle SOC 2, ISO 27001, GDPR, and more - Divot listeners get $1,500 credits to get started: https://delve.co/deals/divot Pulley Manage your cap table with intuitive tools built to help founders make informed decisions without breaking stride. https://tinyurl.com/PulleyPartner Timestamps: 1:27 — Working 7 Days a Week 2:08 — Shaping 100,000+ Boards 4:54 — Surfboard Design Is Logic 5:38 — Every Board Has Tradeoffs 6:07 — 100+ Ways to Shape a Board 7:07 — From 5ft Boards to Big Wave Guns 7:19 — Why Top Surfers Work With Bob 9:47 — Collaboration Beats Guesswork 11:54 — When Mastery Actually Begins 16:04 — Finding Mavericks Before the Hype 18:14 — Chasing Mavericks & Meeting Jay 25:18 — The Iconic Wipeout Explained 29:56 — Injury, Fear & Healing in the Ocean 38:07 — Bells Beach & Teaching in Australia 40:26 — Surviving Sharks in Big Surf 43:58 — Bali Before Surf Tourism 48:20 — How to Handle Conflict in the Water 55:05 — One Idea for the World 1:01:40 — The Mark Bob Wants to Leave Follow Divot: YouTube: https://www.youtube.com/@Divotpod X (Twitter): https://twitter.com/divotdotorg Instagram: https://www.instagram.com/divotpod TikTok: https://www.tiktok.com/@divotpod LinkedIn: https://www.linkedin.com/company/divotdotorg Hashtags: #BobPearson #SurfboardShaping #BigWaveSurfing #Mavericks #ChasingMavericks #SurfingLegends #LairdHamilton #JayMoriarty #SurfDesign #SurfCulture #OceanLife #MentalHealth #Craftsmanship #Mastery #DivotPodcast

    1h 3m
See All (41)

4.9
out of 5
19 Ratings

About

Divot brings you weekly conversations with the people building the future—founders, creators, athletes, and visionaries pushing the limits of business, technology, sports, and entertainment. We go beyond success stories to explore the real moments that define a journey—the risks, the failures, the breakthroughs, and the lessons that can help you on your path. Stories of people making their mark, and how you can too. New episodes every Wednesday. #DivotPodcast #Business #Tech #Sports #Entertainment #Innovation

Information

  • Creator
    Derek Andersen
  • Years Active
    2025 - 2026
  • Episodes
    41
  • Rating
    Clean
  • Copyright
    © Derek Andersen
  • Show Website
    Divot

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